FR2520364A1 - Lithium carbamoyl phosphate(s) - are anti:aggression, sedative, and anticonvulsants - Google Patents
Lithium carbamoyl phosphate(s) - are anti:aggression, sedative, and anticonvulsants Download PDFInfo
- Publication number
- FR2520364A1 FR2520364A1 FR8201348A FR8201348A FR2520364A1 FR 2520364 A1 FR2520364 A1 FR 2520364A1 FR 8201348 A FR8201348 A FR 8201348A FR 8201348 A FR8201348 A FR 8201348A FR 2520364 A1 FR2520364 A1 FR 2520364A1
- Authority
- FR
- France
- Prior art keywords
- formula
- lithium
- acid
- aggression
- phosphoric acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 230000016571 aggressive behavior Effects 0.000 title abstract 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 title description 4
- 229910052744 lithium Inorganic materials 0.000 title description 4
- 229940125681 anticonvulsant agent Drugs 0.000 title 1
- 239000001961 anticonvulsive agent Substances 0.000 title 1
- FFQKYPRQEYGKAF-UHFFFAOYSA-N carbamoyl phosphate Chemical compound NC(=O)OP(O)(O)=O FFQKYPRQEYGKAF-UHFFFAOYSA-N 0.000 title 1
- 239000000932 sedative agent Substances 0.000 title 1
- 230000001624 sedative effect Effects 0.000 title 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 14
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 9
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 7
- 239000012948 isocyanate Substances 0.000 claims abstract description 6
- -1 alkyl isocyanate Chemical class 0.000 claims abstract description 4
- 150000003839 salts Chemical class 0.000 claims abstract description 3
- 230000000903 blocking effect Effects 0.000 claims abstract 3
- 239000003814 drug Substances 0.000 claims description 7
- 229940079593 drug Drugs 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 3
- 150000002641 lithium Chemical class 0.000 claims 1
- 230000007423 decrease Effects 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 4
- 206010010904 Convulsion Diseases 0.000 abstract description 3
- 230000036461 convulsion Effects 0.000 abstract description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 abstract description 2
- 229910003002 lithium salt Inorganic materials 0.000 abstract description 2
- 159000000002 lithium salts Chemical class 0.000 abstract description 2
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 238000002347 injection Methods 0.000 abstract 1
- 239000007924 injection Substances 0.000 abstract 1
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 6
- 229910052808 lithium carbonate Inorganic materials 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 230000004899 motility Effects 0.000 description 4
- QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 150000002513 isocyanates Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 2
- 238000007792 addition Methods 0.000 description 2
- 230000000202 analgesic effect Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 229940076279 serotonin Drugs 0.000 description 2
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 208000028683 bipolar I disease Diseases 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 235000008504 concentrate Nutrition 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000003291 dopaminomimetic effect Effects 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 230000001052 transient effect Effects 0.000 description 1
- 229940086542 triethylamine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3886—Acids containing the structure -C(=X)-P(=X)(XH)2 or NC-P(=X)(XH)2, (X = O, S, Se)
- C07F9/3891—Acids containing the structure -C(=X)-P(=X)(XH)2, (X = O, S, Se)
Landscapes
- Chemical & Material Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
Médicament, utilisable notamment en psychatrie, ut lisant comme principe actif un N-alkyl carba;noylphosphate de lithiun.Medicinal product, usable in particular in psychatria, using as active ingredient an N-alkyl carba; lithium nucleus phosphate.
La presente Invention concerte un nouveau médicament utilisable notamment en psychiatrie. The present invention relates to a new drug usable in particular in psychiatry.
Le médicament selon l'invention est caractérisé en ce qu'il comporte un produit de formule
dans laquelle R est un radical alkyle linéaire ou ramifié et plus particulièrement un radical alkyle inférieur ayant 1 9 4 atomes de carbone, ou un sel pharmaceutiquement acceptable dudit produit de formule (I).The medicament according to the invention is characterized in that it comprises a product of formula
wherein R is a linear or branched alkyl radical and more particularly a lower alkyl radical having 1 9 4 carbon atoms, or a pharmaceutically acceptable salt of said product of formula (I).
Parmi les produits de formule (I), spécialement inté ressuant on mentionnera le composé dans lequel R est CH3. Among the products of formula (I), especially interesting, mention will be made of the compound in which R is CH3.
L'invention concerne également un procédé de préparation des produits de formule I, ce procédé étant caractérisé en ce qu on fait réagir un isocyanate d alkyle sur un acide phosphorique Po H dont deux fonctions acides ont été bloquées. Pour réaliser le blocage de ces deux fonctions acides on peut
- soit réaliser le sel de triéthylamine de l'acide phosphorique que l'on fera réagir avec l'isocyanate
- soit utiliser directement le phosphate dilithique que l'on fait également réagir avec l'isocyanate.The invention also relates to a process for the preparation of products of formula I, this process being characterized in that an alkyl isocyanate is reacted with a phosphoric acid Po H of which two acid functions have been blocked. To block these two acid functions, we can
- or make the triethylamine salt of phosphoric acid which will be reacted with the isocyanate
- Either directly use the dilithic phosphate which is also reacted with the isocyanate.
L'invention concerne enfin les médicaments qui contiennent au moins un produit de formule (I). I1 a été trouvé en effet que les produits de formule (I) avaient une toxicité faible (la DL50 pour la souris et pour le produit de formule I dans lequel R est CH3 étant environ 3 200 mg/kg par voie ) et une activite pharmacologique qui peut s'exprimer comme suit
- diminution et/ou blocage des systèmes dopaminergiques,
- augmentation, au moins transitoire, de la synthèse de la sérotonine,
- pouvoir analgésique, les conséquences de ces actions se retrouvant dans les constatations suivantes
- diminution de l'agressivité,
- diminution de la motilité et de la curiosité,
- protection contre les convulsions.Finally, the invention relates to medicaments which contain at least one product of formula (I). I1 was indeed found that the products of formula (I) had a low toxicity (the LD50 for the mouse and for the product of formula I in which R is CH3 being approximately 3,200 mg / kg per route) and a pharmacological activity which can be expressed as follows
- decrease and / or blockage of dopaminergic systems,
- at least transient increase in the synthesis of serotonin,
- analgesic power, the consequences of these actions are found in the following observations
- decrease in aggressiveness,
- decreased motility and curiosity,
- protection against convulsions.
On voit que les produits de formule I ont une activité
de même type que celle du carbonate de lithium mais avec une intensité
nettement supérieure.We see that the products of formula I have an activity
of the same type as that of lithium carbonate but with an intensity
significantly superior.
Les exemples non limitatifs ci-après illustrent l'in
vention.The nonlimiting examples below illustrate the in
vention.
Exemple 1
Préparation du N-méthyl-carbamoylphosphate de lithium.Example 1
Preparation of lithium N-methyl-carbamoylphosphate.
On dissout 0,1 mole d'acide phosphorique cristallisé
dans 30 ml d'acétonitrile anhydre et on y ajoute 0,1 mole de triéthyl
amine anhydre tout en refroidissant le mélange avec de la glace.0.1 mol of crystalline phosphoric acid is dissolved
in 30 ml of anhydrous acetonitrile and 0.1 mol of triethyl is added thereto
anhydrous amine while cooling the mixture with ice.
On ajoute ensuite progressivement au mélange 0,1 mole
d'isocyanate de méthyle.0.1 mol is then added gradually to the mixture.
methyl isocyanate.
On laisse revenir à température ambiante et on agite
pendant 12 heures, le pH étant maintenu à 6 par addition de triéthyl
amine:
On concentre sous vide, reprend le produit sec par
200 ml d'eau et on neutralise la solution par adjonction de carbonate
de lithium et d'hydroxyde de lithium jusqu'a virage de la phénol
phtaléine.Leave to return to room temperature and stir
for 12 hours, the pH being maintained at 6 by addition of triethyl
amine:
Concentrate under vacuum, take up the dry product with
200 ml of water and the solution is neutralized by adding carbonate
lithium and lithium hydroxide until the phenol changes
phthalein.
Les sels de lithium insolubles sont filtrés et la solu
tion est concentrée jusqu'3 obtention d'un produit pulvérulent.The insoluble lithium salts are filtered and the solu
tion is concentrated until a powdery product is obtained.
On purifie par dissolution (et filtration éventuelle)
dans de l'eau distillée et on précipite la solution obtenue par addi
tion d'alcool éthylique absolu. On filtre et on sèche.It is purified by dissolution (and optional filtration)
in distilled water and the solution obtained is precipitated by addi
tion of absolute ethyl alcohol. It is filtered and dried.
On obtient un produit se présentant sous forme d'une
poudre blanche dont le spectre NMR montre lvexistence d'un doublet centré à 2,55 ppm (TMS) attribuable à NH-CH3 et dont le spectre IR
montre une bande principale à 1750 cm (carbamate).A product is obtained in the form of a
white powder whose NMR spectrum shows the existence of a doublet centered at 2.55 ppm (TMS) attributable to NH-CH3 and whose IR spectrum
shows a main band at 1750 cm (carbamate).
Exemple 2
On a préparé le N-méthyl-carbamoylphosphate de lithium
en réalisant tout d'abord la neutralisation partielle de l'acide phos
phorique avec le carbonate (ou l'hydroxyde de lithium) puis on a fait
reagir sur le produit obtenu, dans un solvant inerte, l'isocyanate de
méthyle. Example 2
We prepared lithium N-methyl-carbamoylphosphate
first of all by partially neutralizing phos acid
phoric with carbonate (or lithium hydroxide) then we did
react on the product obtained, in an inert solvent, the isocyanate of
methyl.
Les propriétés du N-méthyl-carbamoylphosphate de lithium de formule (I) ont été démontrées par les tests suivants réalisés sur des souris et/ou des chiens,
- test concernant l'agressivité induite par des chocs électriques:
dose active 10 MEq par kilo
- test montrant l'activité du produit sur des convulsions produites par un électrochoc
protection de 40% des sujets pour une dose de
5 NEq par kilo
- activité analgésique comparée (test plaque chaude)
avec une dose de 13 hEq par kilo on assure une protec
tion de 42% pour le produit selon l'invention (et de
27% pour le carbonate de lithium)
- test évaluant le blocage des systèmes dopaminergines
- dose active à 100 / 6,75 ISiEq par kilo
- pour le carbonate de lithium on arrive à une dose
active à 50% en utilisant 10,115 '!Eq par kilo
- test sur la sécrétion de sérotonine
- dose active après 24 heures 6,75 iEq par kilo
- pour le carbonate de lithium la dose correspondante
(après 24 heures) serait de 10 hEq par kilo
- test de motilité
- à une dose de 13,5 MEq par kilo, la motilité baisse
de 36%
- pour le carbonate de lithium, à une dose correspondante,
la motilité baisse de 12%.The properties of lithium N-methyl-carbamoylphosphate of formula (I) have been demonstrated by the following tests carried out on mice and / or dogs,
- test concerning the aggressiveness induced by electric shocks:
active dose 10 MEq per kilo
- test showing the activity of the product on convulsions produced by an electric shock
protection of 40% of subjects for a dose of
5 NEq per kilo
- comparative analgesic activity (hot plate test)
with a dose of 13 hEq per kilo we provide protection
42% for the product according to the invention (and
27% for lithium carbonate)
- test evaluating the blockage of dopaminergin systems
- active dose at 100 / 6.75 ISiEq per kilo
- for lithium carbonate we arrive at a dose
active at 50% using 10,115 '! Eq per kilo
- test on the secretion of serotonin
- active dose after 24 hours 6.75 iEq per kilo
- for lithium carbonate the corresponding dose
(after 24 hours) would be 10 hEq per kilo
- motility test
- at a dose of 13.5 MEq per kilo, motility decreases
36%
- for lithium carbonate, at a corresponding dose,
motility drops by 12%.
Ces résultats montrent l'activité certaine des produits de fprmule I et notamment du dérivé de formule (I) dans lequel R est
CH3.These results show the certain activity of the products of formula I and in particular of the derivative of formula (I) in which R is
CH3.
Les médicaments contenant un produit de formule (I) (qui peut éventuellement être utilisé en association avec d'autres produits actifs) sont utilisables notamment en psychiatrie pour le traitement des états maniaco-dépressifs. Medicines containing a product of formula (I) (which can optionally be used in combination with other active products) can be used in particular in psychiatry for the treatment of manic-depressive states.
Ces médicaments sont conditionnés pour être administrés sous forme orale (comprimes, dragés, gélules, sirops), sous forme injectable et contiennent par unité de médication de 250 à 750 mg de produit actif. These drugs are conditioned to be administered in oral form (tablets, dragees, capsules, syrups), in injectable form and contain per unit of medication from 250 to 750 mg of active product.
Claims (6)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8201348A FR2520364A1 (en) | 1982-01-28 | 1982-01-28 | Lithium carbamoyl phosphate(s) - are anti:aggression, sedative, and anticonvulsants |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8201348A FR2520364A1 (en) | 1982-01-28 | 1982-01-28 | Lithium carbamoyl phosphate(s) - are anti:aggression, sedative, and anticonvulsants |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2520364A1 true FR2520364A1 (en) | 1983-07-29 |
| FR2520364B1 FR2520364B1 (en) | 1984-05-04 |
Family
ID=9270414
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8201348A Granted FR2520364A1 (en) | 1982-01-28 | 1982-01-28 | Lithium carbamoyl phosphate(s) - are anti:aggression, sedative, and anticonvulsants |
Country Status (1)
| Country | Link |
|---|---|
| FR (1) | FR2520364A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0129628A1 (en) * | 1983-06-23 | 1985-01-02 | Marcel Richard | Medicine, especially useful in psychiatry, which uses as the active constituent a lithium N-alkylcarbamoyl phosphate |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4063923A (en) * | 1973-07-23 | 1977-12-20 | E. I. Du Pont De Nemours And Company | Carbamoylphosphonic acid brush control agents |
| EP0021391A1 (en) * | 1979-07-03 | 1981-01-07 | Bayer Ag | Phosphonoformic acid hydrazides, process for their preparation and their use as medicines |
-
1982
- 1982-01-28 FR FR8201348A patent/FR2520364A1/en active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4063923A (en) * | 1973-07-23 | 1977-12-20 | E. I. Du Pont De Nemours And Company | Carbamoylphosphonic acid brush control agents |
| EP0021391A1 (en) * | 1979-07-03 | 1981-01-07 | Bayer Ag | Phosphonoformic acid hydrazides, process for their preparation and their use as medicines |
Non-Patent Citations (1)
| Title |
|---|
| EXBK/69 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0129628A1 (en) * | 1983-06-23 | 1985-01-02 | Marcel Richard | Medicine, especially useful in psychiatry, which uses as the active constituent a lithium N-alkylcarbamoyl phosphate |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2520364B1 (en) | 1984-05-04 |
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